Abstract
Tetraphenylmethane (1 ) and several functionalized
tetraphenylmethanes 4 -7 , all of them useful building blocks for
the construction of tetraarylmethane frameworks, are readily synthesized
by improved standard procedures in multigram quantities. The structure
of compound 5 has been additionally corroborated
by an X-ray structure analysis. The novel class of tetrakis(thiazolylphenyl)methanes 8 showing a significant blue emission upon
UV-excitation can be prepared in good yield by Hantzsch synthesis
starting from the tetra(α-bromoketone) derivative 4b .
Key words
acylations - alkylations - cyclizations - dendrimers - heterocycles
References 1 New address: Organisch-Chemisches Institut
der Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer
Feld 270, 69120 Heidelberg, Germany.
2a
Tomalia DA.
Naylor AM.
Goddard WA.
Angew. Chem.,
Int. Ed. Engl.
1990,
29:
113
2b
Hawker CJ.
Fréchet JMJ.
J.
Am. Chem. Soc.
1990,
112:
7638
2c
Berresheim AJ.
Müller M.
Müllen K.
Chem. Rev.
1999,
99:
1747
2d
Schwab PFH.
Levin MD.
Michl J.
Chem. Rev.
1999,
99:
1863
3 For a very recent review on dendrimers,
see e.g.: Fischer M.
Vögtle F.
Angew. Chem. Int. Ed.
1999,
38:
885
For recent and significant contributions
to the synthesis of tetraarylmethanes, see e.g.:
4a
Wilson LM.
Griffin AC.
J.
Mater. Chem.
1993,
3:
991
4b
Sengupta S.
Sadhukhan SK.
Tetrahedron Lett.
1998,
39:
1237
4c
Sengupta S.
Sadhukhan SK.
Tetrahedron Lett.
1999,
40:
9157
4d
Mongin O.
Gossauer A.
Tetrahedron
1997,
53:
6835
4e
Lambert C.
Gaschler W.
Nöll G.
Weber M.
Schmälzlin E.
Bräuchle C.
Meerholz K.
J.
Chem. Soc., Perkin Trans. 2
2001,
964
4f
Zhao H.
Tanjutco C.
Thayumanavan S.
Tetrahedron
Lett.
2001,
42:
4421
4g
Robinson MR.
Wang S.
Bazan GC.
Cao Y.
Adv. Mater.
2000,
12:
1701
5
Eldin S.
Liebman JF.
Reynolds LD.
Dowd P.
Tetrahedron
Lett.
1992,
33:
4525
6a
Constable EC.
Eich O.
Fenske D.
Housecroft CE.
Johnston LA.
Chem.-Eur.
J.
2000,
6:
4364
6b
Constable EC.
Eich O.
Housecroft CE.
Rees DC.
Inorg.
Chim. Acta
2000,
300-302:
158
6c
Constable EC.
Eich O.
Housecroft CE.
J. Chem. Soc., Dalton Trans.
1999,
1363
6d
Cargill Thompson AMW.
Hock J.
McCleverty JA.
Ward MD.
Inorg. Chim. Acta
1997,
256:
331
7
Mongin O.
Gossauer A.
Tetrahedron Lett.
1996,
37:
3825
8
Zimmermann TJ.
Freundel O.
Gompper R.
Müller TJJ.
Eur.
J. Org. Chem.
2000,
3305
9
Yeh H.-C.
Lee R.-H.
Chan L.-H.
Lin T.-YJ.
Chen C.-T.
Balasubramaniam E.
Tao Y.-T.
Chem.
Mater.
2001,
13:
2788
10 Zimmermann, T. J.; Müller,
T. J. J. Eur. J. Org. Chem. 2002 , submitted.
11
Zimmermann TJ.
Müller TJJ.
Z.
Naturforscher
2001,
56B:
1349
12a
Gomberg M.
Ber. Dtsch. Chem. Ges.
1897,
30:
2043
12b
Gomberg M.
J.
Am. Chem. Soc.
1898,
20:
773
13
Ullmann F.
Münzhuber A.
Ber. Dtsch. Chem.
Ges.
1903,
36:
404
14a
Neugebauer FA.
Fischer H.
Bernhardt R.
Chem. Ber.
1976,
109:
2389
14b
Grimm M.
Kirste B.
Kurrek H.
Angew.
Chem., Int. Ed. Engl.
1986,
25:
1097
14c
Su D.
Menger FM.
Tetrahedron Lett.
1997,
38:
1485
14d
Wassmundt FW.
Kiesman WF.
J.
Org. Chem.
1995,
60:
1713
15a
Friedel-Crafts and Related Reactions
Vol.
1:
Olah GA.
Wiley;
New
York:
1963.
15b
Friedel-Crafts
and Related Reactions
Vol. 3:
Olah GA.
Wiley;
New York:
1963.
15c
Schellhammer C.-W. In
Houben-Weyl, Methoden
der Organischen Chemie
Vol. 7/2a:
Müller E.
Georg Thieme
Verlag;
Stuttgart:
1973.
p.15
16 Crystallographic data (excluding structure
factors) for the structure reported in this paper have been deposited
at the Cambridge Crystallographic Data Centre as supplementary publication
no. CCDC-179878 (5 ). Copies of the data
can be obtained free of charge on application to CCDC, 12 Union Road,
Cambridge CB2 1EZ, UK (Fax: +441223/336033; E-mail:
deposit@ccdc.cam.ac.uk).
17
Myrboh B.
Ila H.
Junjappa H.
Synthesis
1981,
126
18a
Verhé R.
De Kimpe N. In
The Chemistry of the Halides, Pseudohalides
and Azides
Suppl. D; Vol. 1:
Patai S.
Rappoport Z.
Wiley;
Chichester:
1983.
p.813
18b
De Kimpe N.
Verhé R. In
The
Chemistry of α-Haloketones, α-Haloaldehydes and α-Haloimines
Patai S.
Rappoport Z.
Wiley;
Chichester:
1988.
p.1
19a For
a recent and comprehensive review on 1,3-thiazoles, see e.g.: Liebscher J. In
Houben-Weyl,
Methoden der Organischen Chemie
Vol. E8b/2:
Schaumann E.
Georg Thieme
Verlag;
Stuttgart:
1995.
p.1
19b
Wiley RH.
Org. React.
1951,
6:
367
19c
Aune JP.
Dou HJ.-M.
Crousier J. In
The Chemistry of
Heterocyclic Compounds
Vol. 34/1:
Weissberger A.
Taylor EC.
Wiley;
New York:
1979.
p.337
20a
Kirstein S.
Möhwald H.
Adv.
Mater.
1995,
7:
460
20b
Wörz O.
Scheibe G.
Z. Naturforscher
1969,
24B:
381
21
Organikum
14
th ed.:
VEB Deutscher Verlag der Wissenschaften;
Berlin:
1993.
22
Hesse M.
Meier H.
Zeeh B.
Spektroskopische Methoden in der organischen
Chemie
Georg Thieme Verlag;
Stuttgart:
1991.
p.69